A two-story house with a balcony, surrounded by lush greenery and trees.

Search Winter Park Cottage Rentals from CA $249

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winter Park cottages

A house with a red door, a front porch, and a pathway leading to the entrance.

1. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $90
CA $249 total
includes taxes & fees
Sep 30 - Oct 1
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

2. The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is CA $223
CA $466 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

3. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is CA $154
CA $335 total
includes taxes & fees
Sep 27 - Sep 28
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A single-story building with the number 297, a red door, and a bench outside.

4. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is CA $121
CA $326 total
includes taxes & fees
Sep 27 - Sep 28
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

5. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $108
CA $309 total
includes taxes & fees
Sep 28 - Sep 29
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $124
CA $300 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

7. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is CA $202
CA $526 total
includes taxes & fees
Sep 30 - Oct 1
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

8. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is CA $297
CA $723 total
includes taxes & fees
Oct 2 - Oct 3
Fire Pit & Yard: Updated Winter Garden Home!
A resort with multiple buildings, a central pool area, and a lake.

9. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is CA $298
CA $635 total
includes taxes & fees
Sep 29 - Sep 30
Th60 - 3BR House Near Disney With Pool Access
A single-story mobile home with a front porch and a small deck.

10. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $120
CA $297 total
includes taxes & fees
Sep 30 - Oct 1
Newly Remodeled Tiny Home 20 minutes from Disney!~
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

11. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is CA $240
CA $1,198 total
includes taxes & fees
Oct 6 - Oct 7
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

8/10 Good
"For the price I paid, I think the room was absolutely worth it and met my expectations. Thank you for the stay, and I wish your hotel continued success and prosperity!"
Igor 2-night trip
Posted less than an hour ago
Wyndham I-Drive Avanti Resort & Conference Center

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
139
Accommodation
429 Cottages
Lowest Price
CA $249
Highest Price
CA $1,198

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between CA $249 and CA $1,198 per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Park with Expedia?
Expedia has some terrific cottages in Winter Park, so start packing for a memorable vacation close to nature. If you have a fixed budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Winter Park?
Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Winter Park near my cottage?
There are tons of superb things to sink your teeth into in Winter Park. Discover well-known attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other must-see's.

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